Leaving Corporate Was Only the Beginning w/ Tracy Medeiros

Have you ever left one job only to realize you brought all of your old habits with you?When Tracy Medeiros lost her father, she and her husband made the life changing decision to move to Hawaii. She planned to continue working for her corporate employer after the move, but when that opportunity fell through, she accepted a new job in Hawaii. A year later, that company planned to lay her off, and instead of starting over, Tracy turned them into her very first client. What began as an unexpected career change eventually became a business dedicated to helping entrepreneurs create companies that support the lives they want to live. In this episode, Tracy shares the story behind her unexpected journey into entrepreneurship and the lessons she learned along the way. We talk about the corporate habits she had to unlearn, why so many successful businesses have messy back ends, how entrepreneurs become the biggest bottlenecks in their own companies, and why redefining success often starts with building systems that create more freedom instead of more work. If you're ready to stop carrying old habits into your next chapter and start building a business that truly supports the life you want, this episode will challenge the way you think about success, freedom, and growth.Connect with Tracy:Medeiros Consulting Substack - https://medeirosconsulting.substack.com/LinkedIn - www.linkedin.com/in/medeirosconsultingInstagram - https://www.instagram.com/medeirosconsulting/Chapters:01:40 Tracy's unexpected path to entrepreneurship05:55 The corporate mindset that followed her10:05 Why boundaries are harder than they seem13:50 What a Business Design Architect actually does18:55 Why successful businesses are often messy22:50 Hiring isn't always the answer27:20 Why systems create more freedom31:45 Letting go of hustle culture35:30 Building a business around your life38:25 Building routines that support your business 40:15 Tracy's advice for scaling with intentionThis podcast is brought to you in partnership with Liz Chapman & COUpcoming Events:Napa Retreat - October 5-8, 2026 - https://laurennajar.myflodesk.com/cetj223rsrGrowth & Connect Events - https://laurennajar.myflodesk.com/hb2a0mwbqwSave 25% with Flodesk - https://flodesk.com/c/OR8VKLLet’s Stay Connected: → Follow Lauren on Instagram: www.instagram.com/laurennajar → Learn more or work with me: www.laurennajar.com → Follow Business Over Cocktails on IG: www.instagram.com/businessovercocktails → Attend Growth & Connect retreats & events: www.instagram.com/growthandconnect🎧 Subscribe & Review: Love the episode? Don’t forget to subscribe, leave a review, and share with a friend who needs a business boost and a good chat over a cocktail.